


Gunpowder, Gelatine

by pinkevilbob



Category: Critical Role (Web Series)
Genre: Alternate Universe, F/M
Language: English
Status: Completed
Published: 2020-02-05
Updated: 2020-02-09
Packaged: 2021-02-27 21:01:45
Rating: General Audiences
Warnings: No Archive Warnings Apply
Chapters: 2
Words: 3,147
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/22572187
Author URL: https://archiveofourown.org/users/pinkevilbob/pseuds/pinkevilbob
Summary: The Dark Lady was nothing like what Caleb had expected. He had been told all about her and her evil line, and how cruel and vile they all were. And Caleb was told all about how he was destined to defeat her and end her evil reign. All his life he was trained for this moment. To sneak into her manor, disguise himself as a mere servant and slay her. But now he was just confused.
Relationships: Jester Lavorre/Caleb Widogast
Comments: 18
Kudos: 93





	1. Chapter 1

**Author's Note:**

> Oh hey, Pink's finally gone back to posting random AUs no one asked for. So, I saw this prompt of "Character A is an evil overlord and Character B is destined to vanquish them" and I had to write it.
> 
> Title comes from "Killer Queen" by Queen.

The Dark Lady sat upon her great bony throne. It was incredibly over the top and garish, but it fitted the look of the evil palace. Personally, Caleb thought that it was all a bit silly. Schooling his face, he approached her carrying a platter of drinks for her to choose from. “My lady.”

A smirk graced her face as she plucked up a champagne flute from the plate. “Thank you,” she said, which was the last thing Caleb expected to hear from the Dark Lady. She then held up her drink to her pet weasel who drank messily from it.

If he was being honest, the Dark Lady was nothing like what Caleb had expected. He had been told all about her and her evil line, and how cruel and vile they all were. And Caleb was told all about how he was destined to defeat her and end her evil reign. All his life he was trained for this moment. To sneak into her manor, disguise himself as a mere servant and slay her. But now he was just confused.

“Caleb,” the Dark Lady said leaning forward. “Can you refill my drink?”

Caleb stared at her. The weasel had only drank a little bit of it. But that wasn’t the strangest part of it. Every time the Dark Lady wanted something, she asked for it. Horrible beings of unspeakable power were not supposed to be so polite.

“Of course, my lady,” Caleb said with a bow. His given name was never Caleb, but it was wise to protect his identity here so he fully embraced the identity of Caleb. He filled the glass back up the couple of milliliters it was missing.

“Tell me Caleb, where are you from?” She was clicking her hoofed feet together and grinning at him. “I bet it has to be super interesting.”

Caleb looked at her. He was prepared for the possibility of someone asking him those sorts of questions and had a complete backstory of his past, but he never expected the Dark Lady herself to be interested in him. “Nein, not really. I was born on the border territories, but there’s not a lot of work there, so I moved to the city to find a better job.”

The Dark Lady looked him over. “And that’s why you talk so different?”

“Ja, it is,” Caleb said. He had a permanent disguise on that made him look like a tiefling and keep suspicion and interest off him, but apparently it was not working well.  
“Hmm,” the Dark Lady said. She gave her weasel more champagne. Caleb was fairly certain that alcohol was bad for mortal weasels, but it may not have been the same case for demonic ones. “Caleb?”

He stiffened. “Yes, my lady?”

“You know that your tail moves all wrong, right?” The Dark Lady wasn’t even looking away from her pet. “Tiefling tails don’t move like that. Even those that didn’t grow up around other tieflings.”

“What do you mean?” It took all his willpower not to freeze with fear. Caleb was taking too long to fulfil his destiny and kill her, but no opportunity had shown itself yet. And if Caleb was being honest with himself, his curiosity about her was getting the best of him. 

She shrugged. “It’s hard to explain to a non-tiefling. Your tail just doesn’t express things the right way.”

Caleb took a step back. “A non-tiefling? My lady, I’ve been a tiefling my whole life.”

“No, you haven’t. So what were you first?” the Dark Lady asked. She suddenly gasped. “Oh, unless, not even you know that and it’s a great mystery of your life and you were polymorphed when you were like super little and now you’re on a journey of self discovery!” As she got more excited, her tail lashed about behind her faster and faster.

Confusion reigned over Caleb for a moment. This was nothing like anything Ikithon had prepared him for. “My lady?”

A frown crossed her face. “But, no, that’s not the case for you, is it?”

“I have no idea what you are talking about,” Caleb said. Slowly, he reached back for his dagger.

“Oh, don’t be like that. I’m just curious. Besides, I don’t think you should have to hide what you are. We won’t hurt you here,” she said. The Dark Lady sounded so sincere, but it had to be an act. “But, if you really don’t want to, you don’t have to tell me.”

Caleb stared at her. He put his dagger back into place. “I don’t know what you’re talking about my lady, but thank you.”

She sprawled out on her throne idly playing with her weasel on her stomach. “No problem. I don’t really understand secrets, but I know they’re important to some people.”

“They certainly are, my lady,” Caleb said. “But I have none from you.”

“You know, I don’t actually believe you. Oh, what if we make it a game?” the Dark Lady said. “Once a day, I get to guess what you might be. But it’s not fair if you don’t get anything in return.” She tugged at her hair thinking. “I know, for every wrong guess, you get one of my rings.”

Caleb paused thinking about it. Rings held no interest for him, but this wasn’t a deal he could turn down. If he did say no, the Dark Lady would be even more suspicious of him and would never trust him. But if it was all a game to her, then she may let her guard down. “Ja, let’s play this game. One guess a day.”

“Okay!” She bit her lip. “Hmm, this is the first one, so I have to make it a really good one. Let’s see, are you an ogre?”

“An ogre?”

The Dark Lady nodded. “Yeah! A super scrawny, short one.”

“Nein, my lady,” Caleb said. “I am not an ogre.”

She pouted as she took off a ring. “Oh, and I was so sure on that one. Here you go,” she said handing Caleb the ring.

“You really don’t have to give me anything,” Caleb said.

“No, I do. It’s part of the game. And you get a bonus with the first round,” the Dark Lady said.

Caleb eyed her warily. “And what is that?”

She grinned showing off her fangs. “You get to call me Jester. ‘My Lady’ is too formal anyways.”

“Jester?” It was too cute of a name for a being of unadulterated evil. But she didn’t seem to be evil at all and she was cute enough for the name. Caleb shook his head. It all had to be a ruse. Ikithon would never lie to him.

“That’s right!” Jester beamed at him.

His heart skipped a beat. He would have to complete his destiny soon before he lost his nerve. That was obvious. But, really, if he waited a few days, he could gather more information on Jester, the Dark Lady, that was. Waiting a week couldn’t possibly do any harm.


	2. Chapter 2

**Notes for the Chapter:**

> So I wasn't certain on continuing this, but the response made me go ahead and do it. Have to admit I only really knew what would happen in the first 500 words and the rest was made up as I went along. I hope you all like it.

Caleb was a mystery. He looked like a tiefling, but it was obvious that he wasn’t really one. Jester couldn’t explain how she first knew that he wasn’t one. There were lots of small hints and clues, but there was no one thing that explained the mystery of him. 

For the last week, Jester had been guessing what he might be and each day she was wrong. Caleb’s pockets must’ve been bulging with rings by now. So far Jester had guessed an ogre, drow, half- drow, five kobolds in a cloak, a minotaur, and a gnome. And every time Caleb just said no. The game was starting to not be fun. It was supposed to be a welcome distraction from the ever present war with the human empire, but now, it was just another thing for her to stress over.

Jester sighed staring at Caleb. “Is there a problem, Jester?” Caleb asked. He was the perfect example of a servant and she couldn’t ask for anyone better, but she wished that he didn’t feel like he had to hide who he was. People should be free to be who they truly are was her opinion on the matter.

“I wish you’d just tell me,” Jester said.

Caleb shook his head with the slightest hint of a smirk. “That would be breaking the rules.”

Jester pouted. “Don’t you already have enough rings?”

“It’s not about the rings.”

“Then what is it about?” Jester asked leaning forward.

Caleb looked away with a serious look on his face. He was very handsome. “It’s complicated.”

Jester frowned. “Do you need help, Caleb? I’m very powerful, you know. I can help you.”

He stared at her and then shook his head. “Nein, you cannot help with this.”

“Caleb, I’m not joking or anything. I’ll help you in any way I can,” Jester said.

“And why would you do that?” he asked. “I’m nothing more than your servant.”

Jester put her hand on his arm. “I want to help you. I like helping people.”

“You wouldn’t say that if you knew what I was,” Caleb mumbled. He pulled his arm away. “You’d never help me if you knew what I am. I’m beyond your help anyways.”

“Caleb?” Jester bit her lip. “Are you something dangerous? Cause even if you are, I still want to help you. We are friends after all.”

Caleb stared at her. “Friends?”

Jester nodded. “Yeah! I mean, we’ve been playing together and you’ve lasted the longest of anyone in your position.”

“Oh,” he said softly.

“Unless you don’t want to be friends,” Jester said. She didn’t have a lot of friends. Just a lot of servants.

Caleb looked at her with a pain in his eyes. “You won’t want to be friends with me if you knew.”

“Caleb, are you-” but she couldn’t bring herself to finish the question.

“Am I what?” Caleb asked.

Jester turned away. “Are you hungry?”

Caleb breathed out a sigh. “That wasn’t what you were going to ask.”

“Well, this game is dumb and boring and no longer fun,” Jester said. “Why are we even playing it?”

“Because you deserve to know that truth.”

Jester turned around and Caleb was no longer a tiefling. Instead there stood a human all pale with red hair. And in his hand was a dagger. “Are, are you here to kill me?” Jester asked.

“Ja,” Caleb said. “That’s why I was sent here.”

“Oh,” Jester said softly and faintly. She knew that she should scream and call for the guards or run, but she just stood there staring at her friend and his dagger. “So you’re going to kill me now?”

Caleb’s shoulders drooped. “I don’t know. I should.”

Jester nodded nervously. “That’s what assassins are for.”

“I’m not an assassin!” Caleb said and then covered his mouth with his hand looking away. “Ending you was supposed to be my destiny.” 

“That doesn’t sound like a happy destiny,” Jester said.

Caleb laughed, but it was hoarse and forced. “I wouldn’t expect you to be happy with it.”

“No,” Jester said, shaking her head. “I meant being told all the time that you exist just to kill someone. That’s sad.”

“I don’t need you to tell me that. I serve my nation, my people,” Caleb said. “I have to kill you for them.” It seemed almost like he was talking to himself more than to Jester.

“Why?”

Caleb took a step back. “Why?”

Jester nodded. “Yeah, why? How does it help people?”

“It, it will end the war. End the suffering of the people,” Caleb said.

Jester bit her lip. “That is a good reason to kill someone. But I don’t want to die.”

“Nobody does. My parents certainly didn’t.” Caleb was shaking now and held up his dagger in a threatening manner.

“I’m sorry,” Jester said.

His dagger trembled in his grip. “What?”

“I’m sorry that you lost your parents. Was it in the war?” Jester asked.

“Ja, it was. They, they were good to me,” Caleb said.

Jester took a step towards Caleb. It was a foolish move, but she did it anyway. “Too many people lost people in the war.”

Caleb nodded. “So I have to do this.” But he lowered his dagger. “Then why can’t I?”

“I don’t know. Oh oh, maybe you’ve fallen in love, Cay-leb!” Jester said.

Caleb blanched. “What?”

Jester nodded grinning. “Yeah, you’ve fallen in love with the country and don’t want us to lose the war anymore than your own nation losing. And now you’re at an impasse.”

“I … wouldn’t phrase it that way, but ja, I’m at an impasse here.” He sheathed his dagger and sat down on the ground. “I’ve failed.”

“I wouldn’t say that Caleb.”

Caleb looked up at her. “My whole life has been dedicated to your death and now I can’t do it. I’m a failure. I can’t go back.” He hugged himself tightly.

Jester knelt down next to him. “Then stay here.”

“I can’t do that either.” Caleb shook his head repeatedly. “I can’t.”

“Why not?” Jester asked.

Caleb stared at her. “I’m your enemy. I’m human. I was sent here to kill you.”

“So?” Jester asked.

“My being here is a crime,” Caleb said.

Jester rolled her eyes. “I make the rules. I can say that it’s okay for you to be here. After all, I am the Dark Lady.”

“Why? Why would you do that for me?” Caleb asked. 

“Cause we’re friends.” Jester placed a hand gently on his arm.

Caleb just sighed. “I could change my mind any day. I could kill you at any time.”

Jester looked him in the eye. “Will you though?”

He looked away. “I,” Caleb paused, “I don’t know. I honestly don’t know.”

“Okay.” Jester got up.

“Okay?” Caleb got up following her. “It’s not okay! I don't want to kill you.”

Jester looked at him. He looked so miserable. “Then don’t.”

“You make it sound so simple, so easy. It isn’t.” Tears began to run down Caleb’s face. “I wish it was, but it isn’t.”

“Give me your dagger.” She held out her hand.

Caleb undid his belt slipping off his dagger and sheath. “Here. Why do you want it?”

Jester took the dagger and threw it out the window. “There! Now you have nothing to kill me with and we can go back to being friends.”

He stared out the window and then began to shake again.

“Caleb? Caleb, are you okay?” Jester asked. Maybe there was a curse attatched to thedggeer.

Caleb looked up at her and he was laughing. “You are truly one of a kind.”

Jester pouted. “What’s that supposed to mean?”

“That you are kind and have a unique way of looking at problems,” Caleb said.

“Well, why shouldn’t I?” Jester asked. “If you always look at things the same way, you always be stuck in the same place.”

Caleb stared at her. “You, you’re actually going to stop this war, aren’t you?”

“I want to,” Jester said softly looking away.

“No, you’re going to do it. I know it,” Caleb said.

Jester’s cheeks grew hot. She risked a glance at Caleb and he had a soft, sad smile on his place. He actually believed in her. Not a lot of people have done before. “Thank you.”

“I’m just speaking the truth,” Caleb said. “So, when are you locking me up?”

“What?!”

Caleb shook his head. “I’ve made an attempt on your life. You can’t have me just going wherever I please. I’m a dangerous man.”

“But you can’t kill me anymore,” Jester said.

“You can’t just expect me to stay here. I’ve revealed what I am,” Caleb said. He waved down at his humanness.

Jester fiddled with the skirt of her dress. “But you can disguise yourself again, right?”

He shook his head. “Nein. I can’t. Once it’s broken, the spell can’t be renewed.”

“And you dropped it for me,” Jester whispered.

“You deserved to know what I am.” He stood so tall and straight, but there was something that felt small about him. Like he needed protecting. “A human can’t just stay in the castle. Not as a servant or even a guest. The only option is prisoner.”

Nervously, Jester bit her lip not daring to look at Caleb. “There’s another option.”

“There couldn’t possibly be,” Caleb said. “And I’m more than willing to pay for my crimes.”

“Um, some would say it’s a punishment. And maybe it’s a bad idea, but there is something we could do,” Jester said.

“And that is?”

Jester took a deep breath and closed her eyes. “You could marry me. No one could question you being here if you were my husband.”

“Your husband?” Caleb asked.

“Yeah, my husband. We could say that it’s a step towards peace. Put my money where my mouth is. If I have a human husband, then it would only make sense that I wish for the war to end,” Jester said.

Caleb grabbed her arm. “You can’t do this. Not for me. I’m not worthy. Not of you or your trust.”

Jester smiled at him. “That’s not for you to decide. It will be the first step to me ending the war.”

“It will be the first step of painting an even bigger target on your back,” Caleb said. “Both sides will think you’re mad. My master will send more people here.”

“Would they kill you?” Jester asked.

He scoffed. “I’m too well trained to be killed like that. But I worry about you.”

“Could you stop them from killing me?” Jester asked.

“Of course, but that’s not what this is about,” Caleb said. “I can’t marry you.”

“And why not?” She was afraid of the answer, but she had to know.

Caleb sighed. “I’m not worthy of you. I’m nothing but an assassin. I’m not worthy of a lady as beautiful or good as you.”

“You really think that?” Jester asked.

“I know that.”

Jester stared at him. Caleb was bent over looking at his hands. “I’m a tiefling. Humans aren’t supposed to like us.”

“And tieflings aren’t supposed to offer humans their lives and then offer to marry them to keep them safe,” Caleb said. “We’re both terrible examples of our races.”

She laughed. “Yeah, we really are.”

Caleb nodded. They shared the silence for a long moment.

“So, will you do it?” Jester asked. “I don’t want to make you my prisoner.”

“I don’t want to be your prisoner either.” Caleb sighed. “Are you certain about this? Marrying a man destined to defeat you and end your reign?”

Jester nodded. “I think so.”

Caleb took a deep breath. “Then yes, I will marry you.” 

“This is going to be great! We’ll be friends and end the war!” Jester said.

He sighed. “This is going to be an interesting union.”

**Notes for the Chapter:**

> ...I'm apparently a big sucker for fantasy royal marriages... This is the fifth time I wrote this trope.


End file.
